Synthesis of 2-halo-2H-azirines from phosphorus ylides

• Author(s): Melo, Teresa M. V. D. Pinho e ; Gonsalves, António M. D'A. Rocha ; Lopes, Cláudia S. J. ; Gilchrist, Thomas L.
• Date: 1999
• Persistent ID: http://hdl.handle.net/10316/5271
• Origin: Estudo Geral - Universidade de Coimbra
• Document Type: Article
• Language: English

Description

[alpha]-Oxophosphonium ylides (3a-3e) react with N-chlorosuccinimide and N-bromosuccinimide in the presence of azidotrimethylsilane giving the corresponding haloazidoalkenes (4a-4g) with elimination of triphenylphosphine oxide. These compounds were completely converted to the 2H-azirines 5a-5g on heating in heptane. http://www.sciencedirect.com/science/article/B6THS-3VXSK6D-3T/1/9eb19b08a4875f23803d57d6eca5b2d2